Ethanol → Ethyl 4-iodobenzoate

HRID 1796953Notes

Reaction equation

HRID 1796953 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:16][CH2:17]O>>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:16][CH3:17])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 120854-Iodobenzoic acid

Product 1

HCID 142891Ethyl 4-iodobenzoate

Procedure

A mixture of 21.0 g of 4-iodobenzoic acid, 100 ml of absolute EtOH and 6 ml of concentrated sulfuric acid was refluxed with stirring for 6 days. At the end of this time the reaction mixture was concentrated by boiling and an additional 4 ml of concentrated sulfuric acid added. The mixture was then refluxed for an additional 11 days, after which the mixture was cooled and 50 g of ice and 150 ml Et2O were added. The phases were separated and the aqueous layer was extracted with Et2O. The combined organic phases were washed with water, sat. aqueous NaHCO3 and water. The organic phase was then dried over MgSO4 and concentrated under vacuum to provide the title compound as a clear brownish liquid.

Workup

  1. temperaturewas refluxed
  2. concentrationAt the end of this time the reaction mixture was concentrated
  3. additionan additional 4 ml of concentrated sulfuric acid added
  4. temperatureThe mixture was then refluxed for an additional 11 days
  5. temperatureafter which the mixture was cooled
  6. addition50 g of ice and 150 ml Et2O were added
  7. customThe phases were separated
  8. extractionthe aqueous layer was extracted with Et2O
  9. washThe combined organic phases were washed with water, sat. aqueous NaHCO3 and water
  10. dry with materialThe organic phase was then dried over MgSO4
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-43b075c0a4bd4fecac15925c73da8f04
Source dataset
uspto-grants-2006_04
Patent number
US07034026B2

Reaction notes

Loading…